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Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group
Author(s) -
Chen ZhengJun,
Liang Wei,
Chen Zhuo,
Chen Lin
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001409
Subject(s) - chemistry , succinimide , pyrrolidine , oxindole , catalysis , cycloaddition , isatin , trifluoromethyl , combinatorial chemistry , organic chemistry , alkyl
An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N ‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s in good yields and with excellent diastereoselectivities. The preparative‐scale reaction in conjunction with the optimized Suzuki–Miyaura cross‐coupling derivatizations of the product give prominence to application prospect of this methodology. The investigation on the reaction mechanism implies that the real catalyst in the cycloaddition might be tetrahexylammonium carbonate.